Isopropanol → [2-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamic acid tert-butyl ester 2,4,6-trimethylbenzenesulfonic acid salt

HRID 2078437노트

반응식

HRID 2078437 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([OH:13])(=[O:12])=[O:11].[C:14]([O:18][C:19](=[O:39])[NH:20][CH2:21][CH2:22][N:23]1[CH2:30][CH:29]2[O:31][CH:25]([CH2:26][N:27](CC3C=CC=CC=3)[CH2:28]2)[CH2:24]1)([CH3:17])([CH3:16])[CH3:15].C(O)(C)C.[H][H]>[Pd].O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[S:10]([OH:13])(=[O:12])=[O:11].[C:14]([O:18][C:19](=[O:39])[NH:20][CH2:21][CH2:22][N:23]1[CH2:24][CH:25]2[O:31][CH:29]([CH2:28][NH:27][CH2:26]2)[CH2:30]1)([CH3:17])([CH3:15])[CH3:16]

참가 물질

6

반응물 3

HCID 3776IsopropanolHCID 10144350[2-(7-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-ethyl]-carbamic acid tert-butyl ester 2,4,6-trimethylbenzenesulfonic acid saltHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 10096310[2-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamic acid tert-butyl ester 2,4,6-trimethylbenzenesulfonic acid salt

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 962Water용매

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온도
73 °C

실험 절차

[2-(7-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamic acid tert-butyl ester 2,4,6-trimethylbenzenesulfonic acid salt (150 g; see Preparation P above), isopropanol (IPA; 225 mL) and water (75 mL) were combined in a metal hydrogenation vessel. Solid 5% Pd/C catalyst (4.7 g, 61% water wet, Johnson Matthey type 440) was added. Hydrogen was introduced to the vessel and stirring was started. The mixture was hydrogenated under 2.5 bar of hydrogen pressure and was simultaneously heated to 55° C. (temperature overshot to 73° C.). Gas uptake measurement showed the reaction to be complete after 1 hour. After cooling to 47° C. the catalyst was removed by filtration through a glass fibre filter paper. The catalyst was washed on the filter with IPA (75 mL) and the combined filtrate and washings used in the next step.

후처리

  1. customthe reaction
  2. temperatureAfter cooling to 47° C. the catalyst
  3. customwas removed by filtration through a glass fibre
  4. filtrationfilter paper
  5. washThe catalyst was washed on the
  6. filtrationfilter with IPA (75 mL)

출처 및 근거

ORD 기록
ord-d145988999dc4d87adc6771193960ac0
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928225B2

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